EP 0131374 A1 19850116 - Process and intermediates for the preparation of penem derivatives.
Title (en)
Process and intermediates for the preparation of penem derivatives.
Title (de)
Verfahren und Zwischenprodukte zur Herstellung von Penem-Derivaten.
Title (fr)
Procédé et intermédiaires pour la préparation de dérivés de pénème.
Publication
Application
Priority
US 50289583 A 19830610
Abstract (en)
[origin: ES8603492A1] Prepn. of penem derivs. of formula (I), or their salts, comprises (a) desulphurising a beta-lactam of formula (VI) to give a cpd. (VII); (b) halogenating to give a cpd. (III); and (c) cyclising to form (I). R = H or 1-2C 1-hydroxyalkyl) (opt. protected); R1 = A-G, A-G1, G1 or CH(G2)2; A = 1-4C alkylene; G = H, 1-5C alkoxy, 2-(1-5C 2-(1-5C alkoxy)ethoxy, 1-5C alkylthio, phenoxy, thiophenoxy, azido, amino (opt. substd. by a protecting gp.), N-phenyl-N-(1-4C alkyl)amino, 2-6C alkanoylamino, 3-10C alkoxyalkanoylamino, 2-(2-6C alkanoylamino)ethoxy, aminocarbonyl, aminocarbonyloxy, 2-5C alkylaminocarbonylamino, 4-7C alkanoylaminoacetylamino, alkylamino carbonyloxy, 2-5C amino carbonyl alkoxy, 2-5C alkylaminocarbonyl or 3-9C N-(alkoxyalkyl)aminocarbonyl; G1 = azetidinyl (opt. substd. by 2-6C N-alkanoyl or amino protecting gp.) or a 5- or 6-membered carbocyclic ring or heterocyclic ring contg. 1-20 or 1-4N or 1S, 1N and 10 or 1N and 1S (both opt. substd. by 1 or 2 1-4C alkyl gps. or 2-5C alkoxycarbonyl gps. or by oxo, NH2, protected amino, aminocarbonyl, 2-7C alkoxyalkyl, phenyl, CHO, 2-5C alkylamino carbonyl(amino), 2-5C alkanoylamino, 1-4C alkoxy, phenoxyacetyl or a heterocyclic N contg. gp. substd. by an amino protectinggp.; G2 = 3-7C alkanoylaminomethyl or 1-4C alkoxy; R2 = H, a ester gp. which can be hydrolysed in vivo or a protecting gp.; X = O or S; R4 = 1-7C alkyl or alkyl substd. by 1-4C alkoxy, phenyl, pyridyl or benzothiazolyl; i = 0 or 1; R5 = Cl, Br or I. (B) Cpds. (VII), (III) and (VI) are new.
[origin: ES8603492A1] Prepn. of penem derivs. of formula (I), or their salts, comprises (a) desulphurising a beta-lactam of formula (VI) to give a cpd. (VII) (b) halogenating to give a cpd. (III) and (c) cyclising to form (I). R = H or 1-2C 1-hydroxyalkyl) (opt. protected) R1 = A-G, A-G1, G1 or CH(G2)2 A = 1-4C alkylene G = H, 1-5C alkoxy, 2-(1-5C 2-(1-5C alkoxy)ethoxy, 1-5C alkylthio, phenoxy, thiophenoxy, azido, amino (opt. substd. by a protecting gp.), N-phenyl-N-(1-4C alkyl)amino, 2-6C alkanoylamino, 3-10C alkoxyalkanoylamino, 2-(2-6C alkanoylamino)ethoxy, aminocarbonyl, aminocarbonyloxy, 2-5C alkylaminocarbonylamino, 4-7C alkanoylaminoacetylamino, alkylamino carbonyloxy, 2-5C amino carbonyl alkoxy, 2-5C alkylaminocarbonyl or 3-9C N-(alkoxyalkyl)aminocarbonyl G1 = azetidinyl (opt. substd. by 2-6C N-alkanoyl or amino protecting gp.) or a 5- or 6-membered carbocyclic ring or heterocyclic ring contg. 1-20 or 1-4N or 1S, 1N and 10 or 1N and 1S (both opt. substd. by 1 or 2 1-4C alkyl gps. or 2-5C alkoxycarbonyl gps. or by oxo, NH2, protected amino, aminocarbonyl, 2-7C alkoxyalkyl, phenyl, CHO, 2-5C alkylamino carbonyl(amino), 2-5C alkanoylamino, 1-4C alkoxy, phenoxyacetyl or a heterocyclic N contg. gp. substd. by an amino protectinggp. G2 = 3-7C alkanoylaminomethyl or 1-4C alkoxy R2 = H, a ester gp. which can be hydrolysed in vivo or a protecting gp. X = O or S R4 = 1-7C alkyl or alkyl substd. by 1-4C alkoxy, phenyl, pyridyl or benzothiazolyl i = 0 or 1 R5 = Cl, Br or I. (B) Cpds. (VII), (III) and (VI) are new.
IPC 1-7
C07D 499/00; C07D 205/08; C07D 405/12; C07D 401/12; C07D 403/12; C07D 413/12; C07D 409/12
IPC 8 full level
C07C 205/42 (2006.01); C07D 205/08 (2006.01); C07D 205/09 (2006.01); C07D 295/088 (2006.01); C07D 401/12 (2006.01); C07D 403/12 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 413/12 (2006.01); C07D 499/00 (2006.01); C07D 499/88 (2006.01); C25D 5/10 (2006.01)
CPC (source: EP KR US)
C07C 205/42 (2013.01 - EP US); C07C 329/00 (2013.01 - EP US); C07D 205/08 (2013.01 - EP US); C07D 205/09 (2013.01 - EP US); C07D 295/088 (2013.01 - EP US); C07D 401/12 (2013.01 - EP US); C07D 403/12 (2013.01 - EP US); C07D 405/12 (2013.01 - EP US); C07D 409/12 (2013.01 - EP US); C07D 413/12 (2013.01 - EP US); C07D 499/00 (2013.01 - KR); C07D 499/88 (2013.01 - EP US)
Citation (search report)
- [Y] EP 0069377 A2 19830112 - HOECHST UK LTD [GB]
- [Y] EP 0051813 A2 19820519 - HOECHST UK LTD [GB]
- [YP] EP 0091576 A2 19831019 - HOECHST UK LTD [GB]
Designated contracting state (EPC)
AT BE CH DE FR GB IT LI LU NL SE
DOCDB simple family (publication)
EP 0131374 A1 19850116; EP 0131374 B1 19881123; AT E38838 T1 19881215; DE 3475306 D1 19881229; ES 533184 A0 19851216; ES 8603492 A1 19851216; HU 194886 B 19880328; HU T36479 A 19850930; IE 58464 B1 19930922; IE 841428 L 19841210; KR 850000449 A 19850227; KR 870000325 B1 19870227; PH 23000 A 19890224; PL 145176 B1 19880831; PL 248115 A1 19850409; PT 78705 A 19840701; US 4619783 A 19861028; YU 100784 A 19861031; YU 43574 B 19890831
DOCDB simple family (application)
EP 84303766 A 19840605; AT 84303766 T 19840605; DE 3475306 T 19840605; ES 533184 A 19840606; HU 222184 A 19840608; IE 142884 A 19840607; KR 840003235 A 19840609; PH 30784 A 19840607; PL 24811584 A 19840608; PT 7870584 A 19840607; US 50289583 A 19830610; YU 100784 A 19840608